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Caitlyn Jenner Talks First Attempt to Transition in the ’80s

Credit: Angela Weiss/Getty Images

We just met Caitlyn Jenner last year, but according to a new clip from the Makers Conference in Rancho Palos Verdes on Tuesday, her transition has been a long time coming. In the video, the 66-year-old opens up about her first attempt at transitioning from a male to a female, back in the ‘80s.

Following two divorces in a five-year period (from Chrystie Scott in 1981 and Linda Thompson in 1986), Jenner had some soul searching to do. “I got a house in Malibu. I basically stayed there for six years. I really started struggling with my identity, about ‘who am I?'” she admitted. “I started doing things to make me feel better about myself, started doing hormones. But yeah, I was a good 36B. I loved them, you know, I thought: ‘This is fabulous. My mission at that point was to transition before I was 40. Got to 39, I just couldn’t go any farther.”

It was at this point, she met her future wife, Kris Jenner. The pair really hit it off and Caitlyn (then known as Bruce) was honest about everything, right from the start. “I had to be,” she said, “I was a 36B.” Once their children, Kendall and Kylie were born, Caitlyn decided to put her family first.

Credit: Ron Galella, Ltd./WireImage

“Everything was heading in the right direction. I made this decision to kind of move on in my life — Kris and I together, and this family,” Caitlyn said. “‘Okay, I’ve got to get rid of these gender things and get off hormones and this and that.’ I actually had my boobs removed. I never told anybody that.”

During their 23 years of marriage, the couple set a few boundaries for Caitlyn’s gender expression. “The rules with Kris and I — don’t dress up, certainly around the house,” she revealed. “If you really need to do that, when you’re on the road, take stuff and do that. So I did that for years.”

Caitlyn and Kris finalized their divorce in December 2014, after more than a year of separation. Though Kris has previously admitted to being upset by her ex’s Vanity Fair interview, the pair has since moved on and are able to cooperatively support their children.